Nitric Acid → 3-Bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine

HRID 1046010Notes

Reaction equation

HRID 1046010 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Cl:16].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]=1[Cl:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 674666933-Bromo-4-(2-chloro-5-fluorophenoxy)pyridine

Product 1

HCID 674628543-Bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridineYield 91.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cold (−10° C.) solution of 3-bromo-4-(2-chloro-5-fluorophenoxy)pyridine (1.98 g, 6.54 mmol) in conc. sulfuric acid (5 ml) was added nitric acid (0.55 ml, 8.69 mmol). The resultant mixture was stirred at the same temp for 20 minutes and was then allowed to warm to ambient temp for 30 min. The reaction mixture was treated with crushed ice, stirred, filtered, washed and dried to provide 3-bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine, (2.08 g, 91% yield) as orange yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.00 (s, 1H), 8.62 (m, 2H), 7.81 (d, J=8 Hz, 1H), 7.23 (d, J=2.5 Hz, 1H); MS (ESI) m/z: 348.9 (M+1H+).

Workup

  1. additionThe reaction mixture was treated with crushed ice
  2. filtrationfiltered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-4867f59f2cd54d4b9726e8e2bbbc8d95
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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